Classifications

• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L23/00—Details of semiconductor or other solid state devices
  • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
  • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
  • H01L23/293—Organic, e.g. plastic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/62—Alcohols or phenols
  • C08G59/621—Phenols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
  • C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/49—Phosphorus-containing compounds
  • C08K5/50—Phosphorus bound to carbon only
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
  • H01L2924/0001—Technical content checked by a classifier
  • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S428/00—Stock material or miscellaneous articles
  • Y10S428/901—Printed circuit
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
  • Y10T428/2852—Adhesive compositions
  • Y10T428/287—Adhesive compositions including epoxy group or epoxy polymer
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31511—Of epoxy ether

Definitions

• the present invention relates to a thermosetting resin composition which exhibits excellent curing property and storage stability and advantageously used in the electric and electronic fields, an epoxy resin molding material using the composition and a semiconductor device using the material.
• epoxy resins used in the field of electric and electronic materials amines, imidazole-based compounds, heterocyclic compounds having nitrogen such as diazabicycloundecene, quaternary ammonium compounds, phosphonium compounds, arsonium compounds and the like various compounds have been used as the curing catalyst.
• this phosphonium salt does not have a specific higher order molecular structure and the ion pair is relatively easily susceptible to the influence of the outside environment, a problem arises in that storage stability decreases when this phosphonium salt is applied to recent sealing materials for semiconductors which uses phenol resin curing agents exhibiting greater mobility of molecules such as low molecular weight epoxy resins and phenol aralkyl resins.
• Japanese Patent Application Laid-Open No. Japanese Patent Application Laid-Open No.
• a curing accelerator which is a molecular association compound of a tetrasubstituted phosphonium compound, a compound having at least two phenolic hydroxyl groups in one molecule and a conjugate base of the compound having at least two phenolic hydroxyl groups in one molecule.
• This molecular association compound corresponds to molecular compound (C) represented by general formula (1) or (2) described in the present invention in which m represents 1,
• this molecular association compound has a problem in that the active site in the reaction is strongly protected by the steric hindrance due to the higher order molecular structure and the curing property decreases although the storage stability is excellent.
• the present invention has an object of providing a thermosetting resin composition which exhibits excellent curing property and storage stability and is advantageously used in the field of electric and electronic materials, an epoxy resin molding material using the composition and a semiconductor device exhibiting excellent reliability under humid conditions.
• the present invention provides
• thermosetting resin composition which comprises as essential components thereof (A) a compound having at least two epoxy groups in one molecule, (B) a compound having at least two phenolic hydroxyl groups in one molecule and (C) a molecular compound represented by any one of general formula (1) and general formula (2); general formula (1) being:
• R 1 , R 2 , R 3 and R 4 each represent a substituted or unsubstituted aromatic group or an alkyl group
• a 1 represents a divalent aromatic group
• B 1 represents a single bond, a divalent group selected from ether groups, sulfone groups, sulfide groups and carbonyl groups or a divalent organic group having 1 to 13 carbon atoms and m represents a number in a range of 0 ⁇ m ⁇ 0.75;
• general formula (2) being:
• R 1 , R 2 , R 3 and R 4 each represent a substituted or unsubstituted aromatic group or an alkyl group
• a 2 represents a divalent aromatic group
• m represents a number in a range of 0 ⁇ m ⁇ 0.75;
• An epoxy resin molding material which comprises as essential components thereof (A) a compound having at least two epoxy groups in one molecule, (B) a compound having at least two phenolic hydroxyl groups in one molecule, (C) a molecular compound represented by any one of general formula (1) and general formula (2) and (D) an inorganic filler; general formula (1) being:
• R 1 , R 2 , R 3 and R 4 each represent a substituted or unsubstituted aromatic group or an alkyl group
• a 1 represents a divalent aromatic group
• B 1 represents a single bond, a divalent group selected from ether groups, sulfone groups, sulfide groups and carbonyl groups or a divalent organic group having 1 to 13 carbon atoms and m represents a number in a range of 0 ⁇ m ⁇ 0.75;
• general formula (2) being:
• R 1 , R 2 , R 3 and R 4 each represent a substituted or unsubstituted aromatic group or an alkyl group
• a 2 represents a divalent aromatic group
• m represents a number in a range of 0 ⁇ m ⁇ 0.75;
• a semiconductor device which comprises a semiconductor element sealed with an epoxy resin molding material described in any one of [2], [3] and [4].
• Compound (A) having at least two epoxy groups in one molecule which is used in the present invention is not particularly limited as long as the compound has at least two epoxy groups in one molecule.
• Examples of compound (A) include epoxy resins and epoxy compounds obtained by reacting epichlorohydrin with hydroxyl group in phenols, phenol resins and naphthols such as epoxy resins of the biphenyl type, epoxy resins of the novolak type and epoxy resins of the naphthalene type; epoxy resins obtained by epoxidation of olefins with peracids such as alicyclic epoxy resins; and compounds obtained by epoxidation of dihydroxybenzenes such as hydroquinone with epichlorohydrin.
• Compound (B) having at least two phenolic hydroxyl groups in one molecules works as the curing agent for the compound (A) having at least two epoxy groups in one molecule.
• Examples of compound (B) include phenol novolak resin, cresol novolak resins, novolak resins modified with alkyl groups (including resins obtained by co-condensation of the double bond of cycloalkenes with phenols in accordance with the Friedel-Crafts reaction), phenol aralkyl resins and resins obtained by co-condensation of naphthols and phenols with compounds having carbonyl group.
• compound (B) is not limited to the compounds described above and any compound in which hydrogen atoms bonded to aromatic rings are substituted with at least two hydroxyl groups in one molecule can be used.
• Molecular compound (C) which works as the curing accelerator in the present invention is represented by any one of general formula (1) and general formula (2) and is a molecular association compound of tetrasubstituted phosphonium and a phenol compound.
• This compound comprises a combination of one tetrasubstituted phosphonium cation, at least one and less than three phenolic hydroxyl groups and one phenoxide anion. It is considered that the positive charge of the tetrasubstituted phosphonium cation is surrounded with at least one and less than three phenolic hydroxyl groups and one phenoxide anion and a stable structure is formed.
• a tetrasubstituted phosphonium ion having substituted or unsubstituted aryl groups and alkyl groups as the substituents is preferable due to stability against heat and hydrolysis.
• Examples of the phosphonium ion include tetratolylphosphonium ions such as tetraphenylphosphonium ion and tetratolylphosphonium ion; triarylmonoalkylphosphonium ions synthesized from triarylphosphines and alkyl halides such as triphenylmethylphosphonium ion; and tetraalkylphosphonium ions such as tetrabutylphosphonium ion.
• Molecular compound (C) used in the present invention has a structure of the phosphonium-phenoxide salt type as described above. This structure is different from the structure of the conventional compounds of the phosphonium-organic acid anion salt type in that, in molecular compound (C), a higher order structure formed with the hydrogen bonds of protons of the phenolic hydroxyl groups surrounds the ionic bond. In the conventional salt, the reactivity is controlled by the strength of the ionic bond alone. In contrast, in molecular compound (C), the ion pair of the active site of the reaction is surrounded by the higher order structure and protected at the room temperature. In the stage of the actual molding, the higher order structure is decomposed and the active site of the reaction is exposed to exhibit the reactivity. Thus, the so-called latent property can be provided.
• Examples of the phenol compound which can, in general, form a molecular compound with the tetrasubstituted phosphonium ion include bisphenols such as bisphenol A (2,2-bis(4-hydroxyphenyl)propane), bisphenol F (4,4′-methylenebisphenol, 2,4′-methylenebisphenol and 2,2-methylenebisphenol), bis(4-hydroxyphenyl) sulfone (bisphenol S), bisphenol E (4,4′-ethybdenebisphenol), bisphenol fluorene (4,4′-(9H-fluoren-9-ylidene)bisphenol), 4,4′-methylidenebis(2,6-dimethylphenol) and bis(4-hydroxyphenyl)methanone; biphenols such as 4,4′-biphenol, 2,2′-biphenol, 3,3′,5,5′-tetramethylbiphenol and 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane; hydro
• These compounds can form coordinated structures represented by general formula (1) or general formula (2) in which the number represented by m can be in the range of 0 to 2 depending on the relative amounts of the tetrasubstituted phosphonium ion and the phenol compound and the structure of the phenol compound.
• phenol compounds are selected among the above compounds so that the number represented by m is in the range of 0 ⁇ m ⁇ 0.75 in the formed coordinated structure represented by general formula (1) or general formula (2).
• the structures of the tetraphenylphosphonium portion and the phenol portion can be confirmed by the measurement of 1 H-NMR and the mass spectrum.
• the value of m in general formula (1) or general formula (2) can be calculated from the integral intensities of the phosphonium portion and the phenol portion obtained by the measurement of 1 H-NMR of the molecular compound in accordance with the following equation:
• P 0 and F 0 each represent the number of proton in one molecule of the phosphonium cation and P 1 and F 1 represent the integral values of the phosphonium cation portion and the total phenol portion in the anion side, respectively, which are obtained by the measurement.
• m in general formula (1) or general formula (2) representing the molecular compound is decided depending on the stability of phenoxy ion, easiness of hydroxyl group for forming the hydrogen bond, steric hindrance and rigidify of the phenol compound and other factors. It is considered from the steireochemical consideration that m can have discrete values such as 0.0, 0.25, 0.33, 0.5, 0.67, 0.75, 1.0, 1.25, 1.33, 1.5 and so on.
• Examples of the phenol compound which is preferable for forming the structure represented by general formula (1) or general formula (2) in which the number represented by m is in the range of 0 ⁇ m ⁇ 0.75 include bisphenol S, 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane, bis(4-hydroxy-3-methylphenyl) sulfone and bis(4-hydroxyphenyl) ether.
• the formed structure is different depending on the relative amounts of the phosphonium compound and the phenol compound used in the synthesis of the molecular compound.
• m in general formula (1) or general formula (2) represents a number in the range of 0 ⁇ m ⁇ 0.75, the higher order structure is easily decomposed and a catalyst exhibiting a greater activity of curing the epoxy resin can be obtained.
• m in general formula (1) or general formula (2) represents a number of 1 or greater, the protection of the active site of the reaction is strong due to the steric hindrance of the phenol compound and the reactivity at the molding temperature decreases.
• Molecular compound (C) can be synthesized in accordance with any of the following processes.
• a hydrogen halide which is, for example, an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide or an organic base such as pyridine and triethylamine
• a solvent such as an alcohol
• a halide of the above tetrasubstituted phosphonium ion dissolved in a suitable solvent is added, the reaction is allowed to proceed and the object compound is separated as the solid component in accordance with a separating operation such as recrystallization and reprecipitation in the last step.
• a tetrasubstituted phosphonium tetrasubstituted borate and the phenol compound are reacted with generation of heat and further reacted in a solvent such as an alcohol under heating.
• the amount of molecular compound (C) used as the curing accelerator in the present invention is in the range of about 0.5 to 20 parts by weight per 100 parts by weight of the total of the amount of compound (A) having at least two epoxy groups in one molecule and the amount of compound (B) having at least two phenolic hydroxyl groups in one molecule which works as the curing agent.
• the total of the amount by mole of the phenolic hydroxyl group in compound (B) having at least two phenolic groups in one molecule and the amount by mole of the phenolic hydroxyl group in molecular compound (C) is in the range of about 0.5 to 2 moles and preferably in the range of about 0.8 to 1.2 moles per 1 mole of epoxy group in compound (A) having at least two epoxy groups in one molecule since the curing property, heat resistance and electric properties are improved.
• the type of the inorganic filler of component (D) used in the present invention is not particularly limited and inorganic fillers conventionally used for sealing materials can be used.
• examples of the inorganic filler include fused and crushed silica powder, fused spherical silica powder, crystalline silica powder, secondary aggregated silica powder, alumina, titanium white, aluminum hydroxide, talc, clay and glass fiber.
• Fused spherical silica powder is preferable. It is preferable that the shape is close to the perfect sphere as much as possible.
• the spherical silica can be used in an increased amount by using powders having different particle sizes.
• the amount of the inorganic filler is in the range of 200 to 2,400 parts by weight per 100 parts by weight of the total of the amount of compound (A) having at least two epoxy groups in one molecule and the amount of compound (B) having at least two phenolic hydroxyl groups in one molecule.
• the amount is less than 200 parts by weight, there is the possibility that the effect of reinforcement with the filler is not sufficiently exhibited.
• the amount exceeds 2,400 parts by weight there is the possibility that fluidity of the molding material decreases and defective filling takes place during the molding. Therefore, such amounts are not preferable.
• the amount of the inorganic filler is in the range of 250 to 1,400 parts by weight per 100 parts by weight of the total of the amounts by weight of compounds (A) and (B) since the degree of moisture absorption of the product obtained by curing the molding material decreases to prevent formation of cracks in solder and viscosity of the molding material in the melted condition decreases to eliminate the possibility of deforming metal wiring inside the semiconductor device. It is preferable that the inorganic filler is mixed well in advance.
• the epoxy resin molding material of the present invention may further comprise various additives in combination with components (A) to (D), where necessary.
• the additive include coupling agents such as ⁇ -glycidoxypropyltrimethoxysilane, coloring agents such as carbon black, flame retardants such as brominated epoxy resins, antimony oxide and phosphorus compounds, low stress components such as silicone oils and silicone rubbers, mold release agents such as natural wax, synthetic wax, higher fatty acids, metal salts of higher fatty acids and paraffins and antioxidants.
• catalysts such as triphenyl-phosphine and 1,8-diazabicyclo(5,4,0)undecene-7,2-methyl-imidazole may be used in combination without any problems as long as the function of molecular compound (C) as the curing accelerator is not adversely affected.
• the epoxy resin molding material of the present invention can be obtained by mixing components (A) to (D) and other additives at the room temperature by a mixer, followed by kneading by a mixing machine such as rolls and an extruder, cooling and pulverizing.
• the molding and curing can be achieved in accordance with the transfer molding, the compression molding or the injection molding.
• the semiconductor device prepared by sealing with the cured product of the epoxy resin molding composition of the present invention is included in the technical range of the present invention and exhibits excellent resistance to moisture.
• thermosetting resin composition and the epoxy resin molding material of the present invention exhibit excellent curing property and storage stability and the semiconductor device obtained by sealing a semiconductor element with the epoxy resin molding material exhibits excellent reliability;under humid conditions. Therefore, the composition, the material and the device are used industrially advantageously.
• a synthesized molecular compound of component of component (C) was reacted with oxalic acid in a known excess amount by weight in a mixed solvent of methanol and water.
• the amount of oxalic acid remaining after the reaction was determined with an aqueous solution of sodium hydroxide having a known concentration by normal and the amount by normal per the unit weight of the molecular compound of component (C) (N/g) was calculated.
• the reciprocal of the obtained value was used as the phosphonium phenoxide equivalent.
• C1 was the object ′compound constituted with the tetraphenyl-phosphonium portion and 4,4′-bisphenol S portion.
• Synthesis Examples 2 to 6 and Comparative Synthesis Examples 1 and 2 essentially the same procedures as those conducted in Synthesis Example 1 were conducted in the conditions shown in Table 1 and compounds C2 to C6, D1, and D2, respectively, were prepared. The results are shown in Table 1.
• D3 was a compound in which tetraphenylphosphonium was ionically bonded to a phenoxide formed by elimination of proton from hydroxyl group of p-phenylphenol in relative amounts by mole of 1:1. D3 was not the molecular compound used in the present invention but an ordinary phosphonium salt.
• D4 was a compound in which tetraphenylphosphonium was ionically bonded to a carboxylate formed by elimination of proton from carboxyl group of benzoic acid in relative amounts by mole of 1:1. D4 was not the molecular compound used in the present invention but an ordinary phosphonium salt.
• a synthesized molecular compound of component (C) was added to a compound of component (A) having at least two epoxy groups and a compound of component (B) having at least two phenolic hydroxyl groups and the resultant mixture was pulverized and mixed. After the obtained mixture was kneaded with melting on a heated plate at 100° C. for 5 minutes, the resultant mixture was cooled and pulverized and a sample of a thermosetting resin composition was prepared. The prepared sample was evaluated in accordance with the following methods.
• the torque of a sample prepared in accordance with the above procedures was obtained by using CURASTOMETER (manufactured by ORIENTECH Co., Ltd.; JSR CURASTOMETER PS type) after 45 seconds at 175° C.
• the torque obtained using CURASTOMETER is a parameter indicating the curing property. The greater the value, the more excellent the curing property.
• the unit is kgfcm.
• the initial heat generated by curing immediately after being prepared and the heat generated by curing after storage at 40° C. for 3 days were measured.
• the residual fraction of the heat generated by curing (mJ/mg) after the storage based on the initial heat generated by curing (mJ/mg) was calculated and expressed as the percentage.
• the heat generated by curing was measured in accordance with the differential scanning calorimetry at a rate of temperature elevation of 10° C./minute. The greater the obtained value, the more excellent the storage property.
• thermosetting resin compositions of the present invention exhibited excellent curing property and storage property as shown by the results of Examples.
• the resin composition of Comparative Example 1 using triphenylphoshine as the curing accelerator exhibited poor curing property and storage property.
• the compositions of Comparative Examples 2 and 3 in which the molecular compounds represented by general formula (1) whose m represents 1 were used exhibited a poor curing property.
• the compositions of Comparative Examples 4 and 5 using the phosphonium salts which were not the molecular compound used in the present invention exhibited a poor storage property although the curing property was excellent.
• the resultant mixture was cooled and pulverized and an epoxy resin molding material was obtained.
• the obtained epoxy resin molding material was evaluated in accordance with the following methods. The results are shown in Table 3.
• the spiral flow was measured by using a mold for measuring the spiral flow in accordance with the method of EMMI-I-66 at a mold temperature of 175° C., an injection pressure of 70 kg/cm 2 and a curing time of 2 minutes.
• the spiral flow is a parameter showing the fluidity. The greater the value of the spiral flow, the more excellent the fluidity.
• the unit is cm.
• the reliability under humid conditions was measured in accordance with the following procedures.
• a 16 pDIP was prepared by molding at a mold temperature of 175° C., a pressure of 70 kg/cm 2 and a curing time of 2 minutes. After the molded product was post-cured at 175° C. for 8 hours, a voltage of 20 V was applied to the 16 pDIP in steam at a temperature of 125° C. under a relative humidity of 100% and the product was examined with respect to the broken wiring. The time before the broken wiring was found in 8 or more packages among 15 packages was used as the defect time. The unit is hour. The maximum time of the measurement was 500 hours. When the number of the defective package after 500 hours was 7 or less, the defect time was expressed as 500 hours or longer. The longer the defect time, the more excellent the reliability under humid conditions.
• Example 7 8 9 Formulation (part by weight) component (A) YX-4000H 1) 52 52 52 component (B) XL-225 2) 48 48 48 component (C) type C1 C2 C6 amount 2.9 2.9 2.6 component (D) (fused 500 500 500 spherical silica) other components carbon black 2 2 2 epoxy resin of the 2 2 2 brominated bisphenol A type carnauba wax 2 2 2 2 Properties spiral flow (cm) 105 103 108 torque in curing (kgf ⁇ cm) 80 83 84 residual fraction of flow (%) 84 86 88 reliability under humid >500 >500 >500 condition (hour)
• the epoxy resin molding materials of Examples 7 to 9 of the present invention exhibited remarkably excellent storage property and curing property. It is also shown that the semiconductor devices sealed with the cured products of these epoxy resin molding materials exhibited excellent resistance to moisture. In contrast, the epoxy resin molding materials of Comparative Examples 6 to 10 exhibited the curing property, the fluidity, the storage property or the reliability under humid conditions inferior to that of the epoxy resin molding materials of Examples 7 to 9.

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